The best tip I can give is don’t make it about ‘you’ or ‘him/her’. Base the argument upon why it’s good for the business, team etc. I try to avoid saying ‘but I think we should...’, instead I opt for ‘I’m hearing from the team / the numbers suggest’. At the end of the day it’s about presenting a lot of facts. But if your manager still disagrees make sure you understand his/her reasons - disagree and commit to their decision. If you feel that they are continually overriding you at every decision and don’t believe in most of their decisions then move on.

This doesn’t work in extreme political environments, where they don’t really care about company/stock performance. They’ll let go even star performers and maintain that there were managed out for Company’s sake, even when the employee is voluntarily quitting.

In software, most disagreements aren’t between wrong and right as much as they are one set of benefits over another. Make sure you are both on the same page in terms of priorities that drive decisions. It sounds like you generally aren’t seeking to understand your manager’s motivations or priorities. First seek that out, then you can talk to why your solution is better in terms they will care about.

Trust me, unhappy or stubborn engineers do make a manager’s life difficult. Usually this is a day to day difficulty rather than a monetary difficulty. You shouldn’t aim to make your manager’s life difficult as it naturally makes them less likely to want to help you when it matters - defending you, unblocking you, providing you worthwhile feedback to grow your career, finding opportunities for you to grow and shine, etc.

Yes. It 100% depends on the topic. If about compensation, show other offers to demonstrate market value. If about business decision, that should be pretty obvious that you can dig into assumptions in the business case.

Show other offers? Why? Why not “accept” other offers? If I have to wait to show other offers to get salary bump, that is right there a huge failure of my manager. I hope you are not a manager at Tesla. Because you sound like the kind of manager I would want to avoid (given that you are a manager. Otherwise my apologies :) )

I have similar issues. After trying various things and failing, I've decided to let him be, and I avoid raising concerns to avoid confrontation or conflict with him. It sucks, but I'm living a happier life tbh